Josh pulled his Ford Taurus into his family’s driveway as quietly as he could, it was already midnight after all and he didn’t want to wake anyone up. The gravel lining the driveway crunched loudly beneath his shoes but he didn’t see any lights turn on within the house so he guessed everyone was still asleep. He entered from the back door and headed towards the kitchen to grab a midnight snack when he heard creaking steps. Josh hurriedly put his keys on the hook and headed for the stairs in hopes of avoiding punishment.
“Well, well, well, what do we have here?” came from the stairwell.
“Nothing. Time for brats to sleep anyway,” said Josh.
“But, brother dearest, how does that fit with the facts? You’re home late and I’m all out of mercy after that brat comment,” said Josh’s sister, Rose.
“What do you want, Rose?” asked Josh. “I can’t get punished this close to Halloween and lose the chance to go out tomorrow night.”
“Nothing much — just drive me to Jessica’s house tomorrow and buy me one of the fancy cakes everyone has been talking about since they came to town.”
“Deal. Chocolate as always, right?”
“You know me too well, broski.”
“Good night, Rose, get some rest.”
“Oh, I will after I get some water.”
Josh quickly began the trudge upstairs, thinking about his day. His 5’11” or 180 cm frame filling the hallway. He quickly divested his standard outfit of jeans and a t-shirt into his laundry basket before falling asleep to the noises of creaking branches. When he woke up the next day, he was surprised to see Rose standing in his room by the door. “What are you here for?” he asked sleepily.
“Just wanted to remind you of your promise yesterday!” she exclaimed bubbly. “Don’t think you’ll get to wiggle out of it this time.”
“Yeah, yeah,” he yawned back at her. “I’ll take you over to Jessica’s around 7 PM, OK?”
“That works for me. See you then, bro.”
“Good, now get out. Some of us need our privacy in the morning.”
“If you’re talking about your morning wood, don’t worry about that. It was clearly poking out of your boxers from before we even started our conversation.”
“Get out!” he yelled. She quickly closed his door with a glimmer of mirth in her eyes and stepped away from the fuming teenager before things could escalate further. Josh sighed into his hand and started the process of actually waking up by wiping the crust from his eyes. He turned to his mirror and admired what he saw there for a little bit. His tousled brown bed-hair, bulging muscles in a tank-top shirt, and somewhat tight boxers outlining his semi-hard package. He was a fine specimen if he did say so. He quickly added some shorts to his outfit and headed downstairs to grab some breakfast.
All Hallow’s Eve left the household with lots of sweets from pancakes to french toast for the feast before him. He quickly took a stack of flapjacks and some syrup for himself before setting his plate down next to his sister. Rose took a swipe with her fork at his pancakes and came away victoriously with a forkful of delicious goodness.
“Hey! Lay off the pancakes, this is neutral territory.”
“Sorry, brother dear. Just had to try some,” she smirked back knowing he couldn’t do more while their parents were awake and nearby.
“Children, calm yourselves. There’s plenty more coming down the pipeline,” said their mother, Sarah.
“Fine, mom,” came the twin replies to her intervention.
“So, Rose, what are you and Jessica up to tonight?” asked Sarah. “Going trick or treating as the twins from The Shining again?”
“Nah, this year we’re going as something special,” she said with a hint of mischief in her eyes. “Afraid we can’t spoil the surprise just yet.”
“Can’t be that great,” came quietly from Josh’s lips.
“Just you wait, brother, we’ll get your jaw to drop all night long.”
“I doubt that,” he said more confidently.
“We’ll see about that, Josh,” she replied just as strongly.
“Children… behave.”
Josh finished up his breakfast and went back to his room. He had a whole day to spend relaxing before he had to get ready for the party tonight. Deciding to spend his time playing League of Legends with some friends, he put his little sister out of mind and focused on gaming. By the time he finished up his last game, it was nearly 7 PM and he needed to prepare his costume. This year he was going as Jango Fett and he even had a cool voice changer installed that gave him the accent of the character. He was about to put his costume on when Rose came knocking at his door while holding a dress bag.
“Hey, bro, it’s almost time to head over to Jessica’s place.”
“Oh, right, I almost forgot about that. One second,” he put back his costume into its cover and hopped into some pants. He figured he could drop his little sister off first before heading to his buddy James’s place and change there. “So where is the ‘special’ costume I heard so much about?”
“I’ll show it to you later. It needs to be appreciated in full so Jessica and I promised to help each other put it on when we met up.”
“Sure, chicken.”
“Whatever. Just take me to her place already and we can get half of our arrangement over with. Don’t think I’ve forgotten about my cake by the way!”
“Yeah, yeah, let’s get going squirt.”
Dropping his little sister off went by without much fanfare. He just wished he got to see Jessica, that hot little minx again, but he was in too much of a rush tonight. He headed over to James’s house and changed into his Jango Fett outfit. The party was going to begin in an hour, so he and James drank a few strong beers down in the meantime. Josh didn’t really appreciate the flavor of the alcohol, but he was only looking for the buzz anyway so it was of no consequence to him. After his fourth beer, people began to trickle into the house wearing outfits of all kinds. He saw pirates, cowboys, sexy witches, cute nurses, and more all dancing in the same room.
It was shaping up to be a classic Halloween party when he noticed a girl wearing something out of the ordinary. She had on a golden gown with a black masquerade mask covering a good chunk of her face. She wore blue high heels which lifted her up to a small 5’5″ or 165 cm and had gorgeous dirty-blonde hair wrapped in tresses around her head. He was struck by how beautiful her outfit was even though it didn’t really match the looks of the typical Halloween costume. Josh decided to approach her and see if she might be interested in dancing or maybe something more.
“Hey, there. Fancy a dance?” came out in a sexy New Zealand accent, courtesy of his Jango Fett voice changer.
“Depends on who’s asking,” came back a teasing reply with a lilting Southern accent.
“You can call me ‘Jango’, miss.”
“Ooh, that’s how you want to play it. Well, then call me ‘Sandra’,” she said with a quick smile and finger quotes around the name Emma.
“Sandra, what a beautiful name for a young woman like yourself. Must be hard beating off so many male suitors.”
“Well, actually, would you believe that you’re the first to approach me? All the guys I’ve seen have been going after the more provocative outfits in hopes of scoring fast and easy.”
“What a shame. Because what I see here wouldn’t look nearly as nice lying on the floor. In fact, if I had it my way, I’d see you never removing that dress for any reason except for me.” She flushed with arousal at that statement.
“Well, that’s quite the strong argument in favor of perhaps checking out a private room.”
They walked upstairs together, pausing for the various shenanigans of other party-goers as appropriate before reaching an empty bedroom. It looked like a guest bedroom with clean pastel colors decorating its walls and furniture. Josh quickly stepped behind Sandra and prepared to remove her dress entirely. He placed her golden gown over on a chair and started to place his fingers down her exposed back, watching as she shivered from the touch of his cool fingers. He was about to take off his helmet when she stopped him and said, “Leave it on. I’ll leave on my mask too and this can be our shared little secret.”
“OK,” he said back. “As you wish, milady.”
He dropped his costume’s trousers and exposed his rock hard cock to the cool air. It was slowly engulfed by Sandra’s warm, soft hands as she stroked carefully to ensure maximum pleasure. Josh was already in heaven from this brief interaction but he wanted to return the favor so he lowered her panties and slowly began to play with her wet pussy. He had felt the warmth of her muff through her panties, but fully exposed to the air, he was shocked at just how hot and slick her pussy was. He couldn’t wait to explore further when he noticed a wall within her tight hole. Must be her hymen, he thought absently, a little surprised that someone as beautiful as her was still a virgin.
As the two teens played with the genitals of their partner, they both began to understand what this was heading towards full-on penetration. Josh wanted to make sure she had enough lubrication to ensure maximum pleasure for both parties. He rubbed her clit softly in concentric circles and explored everything he could with his curious fingers. Finally, he decided she was ready for an attempt. He gripped his cock into his fists and aimed it towards Sandra’s pussy. She looked up at him with her baby blue eyes and prepared herself to be penetrated.
“Be gentle, please.”
“I will.”
“Ahh,” she moaned as he entered her pink velvety flesh.
“Just hold on, we’ll make it through this together, Sandra.”
He pushed through her hymen and took her virginity. He paused here to give her time to acclimate to the fullness of experiencing a man’s member fully inside of herself and focused on playing with her C-cup breasts to help the pain subside. He slowly teased her nipples to full rigidity and tweaked them back and forth, twisting a little bit as he did so. Each second that passed inside her excruciatingly tight warmth left him desperate to begin thrusting but he held on until she acknowledged that she was fine. Finally, she said, “I think the worst of it is gone. Let’s continue.”
“Alright, glad to hear that. I don’t think I could have waited much longer.”
He began to thrust inside her pussy carefully trying to maintain a pace that would be agreeable to both of them. Each thrust left them closer and closer to full insertion until finally his entire dick was inside of Sandra. Josh couldn’t have been more pleased with himself given how well the evening had gone already. But he reached up to caress her face while holding her body up with his other arm. She leaned into his touch and the smoldering gaze of her eyes made his cock twitch. He was approaching his first orgasm but before that happened he wanted to confirm a couple of things.
“Are you on birth control?” he asked.
“Yes,” she grunted out as he thrust into her.
“Great because I’m about ready to cum for the first time tonight.”
“Cum inside me! I want to feel your seed splatter my walls.”
“Your wish is my command!” his reply came as he unloaded a torrent of jizz into her tubes.
“OHH, YESS!”
The aftermath of their simultaneous orgasms was a pair of happy, sticky teens with few boundaries left between them. Josh was about to fall asleep at first when he realized his dick was still at least a semi. Maybe he could convince ‘Sandra’ to play again tonight or some other time at least. “That was absolutely amazing, Sandra. I just find myself curious about what my partner looks like under the mask, which I’m sure you feel the same way.”
“Well, it’s true you were a true gentleman and I enjoyed it very much, but I’d like to keep our little secret to a one-time thing. Don’t want any rumours to spread around about me if you knew who I was.”
“Fair enough. Can I interest you in another round then?”
“Nope, my pussy’s feels like it’s been jackhammered all night. Thanks for the offer, champ.” She got up from the bed and walked bow-legged over towards her golden gown. “Could use some help here to zip up the gown.”
Josh got up and walked over to her side, then proceeded to carefully lift the zipper of her dress up all the way. She put back on her blue high heels and headed for the door. “Goodbye, ‘Jango.'” she said with a smile on her face.
“Bye, ‘Sandra,'” he said with a goofy grin on his face still covered by the Jango Fett mask. He slowly put back on his costume and headed out of the room. He told James about his lucky experience that night and reminded him to wash the bedsheets tomorrow morning. Then Josh went home and crashed after his sexual exertions. He was about ready to fall asleep when he heard a car pull up to the house and drop off someone. Must be my sister, he thought. Nothing too important there so he went to the land of dreams which were filled with a beautiful dirty blonde girl on this particular night.
The next morning Josh woke up and grinned to himself as he was brushing his teeth. He couldn’t stop the cheeky little grin he had from getting laid with a cutie. Too bad she hadn’t wanted more or to know who her partner really was, but he’d take what he could get. He headed downstairs to see his little sister, Rose, sitting gingerly at the table. He wondered what that was all about before grabbing some french toast from his smiling mom.
“Hello, sweetie, I was just listening to Rose’s adventures from last night. Come join us.”
“I’ll pass, ma.”
Normally that sort of response would have led to a small argument between himself and Rose, but for some reason, she didn’t bite this morning. “Whatever. Anyway, mom, I met the coolest guy. We danced for a while and kept it all true to my costume — a masquerade ball style meeting.”
“Masquerade?” Josh mumbled a bit confused at what he was hearing from his sister. There’s no way she means me, right? There’s gotta be dozens of people that meet without revealing their true faces or names during an event like Halloween. Out of curiosity, though, he had to confirm something. “What was his costume?” he asked off-hand.
“Thought you weren’t interested, mister big shot? Well, for your information, he was wearing a Jango Fett costume,” she replied back with a smirk.
“Oh, dear God, no,” he said quietly to himself. He had seemingly fucked his sister inadvertently because they were too committed to their costumes. He nearly spat out his breakfast right there but managed to keep it down with some effort. He quickly placed his plate in the sink and left the room. He had some thinking to do because, God help him, of course his stupid dick would still want his dirty blonde angel not caring one bit about a little thing called incest. For now, he’d just do his best to act “normal” around her as much as possible. One thing’s for certain, he was never wearing a mask while fucking someone again.
Added by ShyKite
